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以三苯基膦为母体骨架,设计合成了在苯环上连有环状仲胺取代基的五种新型P,N-配体(L1~L5),利用核磁共振谱(1H,13C,31p)、红外光谱、高分辨质谱和X射线单晶衍射等对配体进行了表征,并将它们应用于Pd催化的C-N键偶联反应中.结果表明,三(2-吗啉基苯基)膦(L5)与三(二亚苄基丙酮)二钯(Pd2(dba)3)组成的体系可有效催化芳基溴代物与仲胺的偶联反应,当以Pd2(dba)3(1 mol%)为催化剂前体、L5(6 mol%)为配体、叔丁醇钠(1.4 mmol)为碱、甲苯为溶剂时,溴代芳烃与仲胺的偶联反应在100℃下可顺利进行,最高分离收率达到95%.

参考文献

[1] Muci A R;Buchwald S L .[J].Topics in Current Chemistry,2002,219:131.
[2] Kantchev E A B;O'Brien C J;Organ M G .[J].Angewandte Chemie International Edition,2007,46:2768.
[3] Aubin Y;Fischmeister C;Thomas C M;Renaud J L .[J].Chemical Society Reviews,2010,39:4130.
[4] Lundgren R J;Stradiotto M.[J].Angewandte Chemie International Edition,2010:498686.
[5] Surry D S;Buchwald S L .[J].Chemical Science,2011,2:27.
[6] Maiti D;Fors B P;Henderson J L;Nakamura Y Buchwald S L .[J].Chemical Science,2011,2:57.
[7] Ley S V;Thomas A W;Angew Chem .[J].International Education Journal,2003,42:5400.
[8] Zhang, H;Cai, Q;Ma, DW .Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles[J].The Journal of Organic Chemistry,2005(13):5164-5173.
[9] Rao, HH;Fu, H;Jiang, YY;Zhao, YF .Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2-phosphonate as the new ligand[J].The Journal of Organic Chemistry,2005(20):8107-8109.
[10] Zhang ZJ;Mao JC;Zhu D;Wu F;Chen HL;Wan BS .Highly efficient and practical phosphoramidite-copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles[J].Tetrahedron,2006(18):4435-4443.
[11] Liu Y F;Bai Y J;Zhang J;Li Y Y,Jiao J P,Qi X L.[J].European Journal of Organic Chemistry,2007:6084.
[12] Altman RA;Buchwald SL .Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines[J].Organic letters,2007(4):643-646.
[13] Cheng DP;Gan FF;Qian WX;Bao WL .D-Glucosamine - a natural ligand for the N-arylation of imidazoles with aryl and heteroaryl bromides catalyzed by CuI[J].Green chemistry,2008(2):171-173.
[14] Wang HF;Li YM;Sun FF;Feng Y;Jin K;Wang XN .1,2,3,4-Tetrahydro-8-hydroxyquinoline-Promoted Copper-Catalyzed Coupling of Nitrogen Nucleophiles and Aryl Bromides[J].The Journal of Organic Chemistry,2008(21):8639-8642.
[15] Xi, ZX;Liu, FH;Zhou, YB;Chen, WZ .CuI/L (L = pyridine-functionalized 1,3-diketones) catalyzed C-N coupling reactions of aryl halides with NH-containing heterocycles[J].Tetrahedron,2008(19):4254-4259.
[16] Tao C Z;Li J;Fu Y;Liu L Guo Q X .[J].Tetrahedron Letters,2008,49:70.
[17] Monnier F;Taillefer M;Angew Chem .[J].International Education Journal,2009,48:6954.
[18] Das, P;Sharma, D;Kumar, M;Singh, B .Copper Promoted C-N and C-O Type Cross-Coupling Reactions[J].Current organic chemistry,2010(8):754-783.
[19] Meng, F.;Zhu, X.;Li, Y.;Xie, J.;Wang, B.;Yao, J.;Wan, Y. .Efficient copper-catalyzed direct amination of aryl halides using aqueous ammonia in water[J].European journal of organic chemistry,2010(32):6149-6152.
[20] Li L Y;Zhu L;Chen D G;Hu X L,Wang R H.[J].European Journal of Organic Chemistry,2011:2692.
[21] Huang, Y.-B.;Yang, C.-T.;Yi, J.;Deng, X.-J.;Fu, Y.;Liu, L. .Cu-catalyzed carbon-heteroatom coupling reactions under mild conditions promoted by resin-bound organic ionic bases[J].The Journal of Organic Chemistry,2011(3):800-810.
[22] Desmarets C.;Schneider R.;Fort Y. .Nickel (0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines[J].The Journal of Organic Chemistry,2002(9):3029-3036.
[23] Liu C;Shen D M;Chen Q Y .[J].Journal of Organic Chemistry,2007,72:2732.
[24] Manolikakes G;Gavryushin A;Knochel P .An efficient silane-promoted nickel-catalyzed amination of aryl and heteroaryl chlorides[J].The Journal of Organic Chemistry,2008(4):1429-1434.
[25] Taillefer M;Xia N;Ouali A .[J].Angewandte Chemie International Edition,2007,46:934.
[26] Correa A;Bolm C;Angew Chem .[J].International Education Journal,2007,46:8862.
[27] Anderson K W;Tundel R E;Ikawa T;Altman R A,Buchwald S L .[J].Angewandte Chemie International Edition,2006,45:6523.
[28] Old DW.;Buchwald SL.;Wolfe JP. .A highly active catalyst for palladium-catalyzed cross-coupling reactions: Room-temperature Suzuki couplings and amination of unactivated aryl chlorides[J].Journal of the American Chemical Society,1998(37):9722-9723.
[29] Old D W;Harris M C;Buchwald S L .[J].Organic Letters,2000,2:1403.
[30] Anderson KW.;Mendez-Perez M.;Priego J.;Buchwald SL. .Palladium-catalyzed amination of aryl nonaflates[J].The Journal of Organic Chemistry,2003(25):9563-9573.
[31] Verboom W;Reinhoudt D N;Visser R;Harkema S .[J].Journal of Organic Chemistry,1984,49:269.
[32] Whited M T;Rivard E;Peters J C.[J].Chemical Communications,2006:1613.
[33] Wolfe JP.;Sadighi JP.;Yin JJ.;Buchwald SL.;Tomori H. .Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates[J].The Journal of Organic Chemistry,2000(4):1158-1174.
[34] Kuwano R.;Utsunomiya M.;Hartwig JF. .Aqueous hydroxide as a base for palladium-catalyzed amination of aryl chlorides and bromides[J].The Journal of Organic Chemistry,2002(18):6479-6486.
[35] Yang C T;Fu Y;Huang Y B;Yi J,Guo Q X,Liu L .[J].Angewandte Chemie International Edition,2009,48:7398.
[36] Basu B;Paul S;Nanda A K .[J].Green Chemistry,2009,11:1115.
[37] Huang X H;Anderson K W;Zim D;Jiang L Klapars A Buchwald S L .[J].Journal of the American Chemical Society,2003,125:6653.
[38] Berman A M;Johnson J S .[J].Journal of Organic Chemistry,2005,70:364.
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